Those were the words Leah Finnegan once used to silence her critics. On Twitter. In the comments section of Gawker, the website where she spent three years building a reputation as an enfant terrible. Even in conversations with people, where she would occasionally pronounce “lol” as a word (something close to “lahl”) and sometimes, if she wanted to underscore its impact, would spell it out.

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“L-O-L,” she says, tracing the letters with an index finger, the way she says she did in her mother’s face at a particularly contentious family funeral.

Looking back on it now, Finnegan says that it was all an elaborate defense mechanism, aimed at people too stupid to get jokes. She’s been couch surfing at various friends’ apartments since being quietly fired from Gawker for her coverage of a recent national tragedy. The post, which she says was a satire of shows that critique stars’ fashion choices at awards shows, was quietly pulled after complaints from many, who argued that a memorial service was not an appropriate target for humor. Several of the dead’s families had complained in particular about her decision to include photos from their Facebook pages.

“At first, I was like, if you don’t want people to make fun of you, don’t dress like a clown, you know?” Finnegan said. “But then I was like, I can see why somebody might be upset, especially if it was their family member who died like that. After dressing like a clown.”

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At that point, Ms. Finnegan spilled the beer she had been drinking on her friend’s couch. When the friend, who declined to be named for this story, asked her to clean it up, Ms. Finnegan replied, “YOLO, bitch!” After the friend left the room in disgust, Ms. Finnegan added, “Great. Now I’m probably going to have to find a new place to stay. Jesus Christ, these fucking people.”

It’s been a rough six months for Ms. Finnegan, 26. After her abrupt ouster from Gawker Media, she says that she assumed she would be able to find another job quickly. She was so confident, she says, that she never even considered changing her LinkedIn profile picture, which features her making an offensive hand gesture to a Photoshopped Mother Teresa. “I figured my future employers should know what they were getting,” said Ms. Finnegan, adding that, in retrospect, while she mostly stands by her choice of picture, if she had to do it over again she would have used a picture of the Teresa taken while she was still alive.

Ms. Finnegan joins a growing cast of former Gawker Media employees whose online personae are built around aggressive honesty and petulance. Her story—both its rise and fall—mirrors that of fellow Gawker alumnus Brian Moylan. Mr. Moylan’s brief freelance career with Entertainment Weekly came to an abrupt end after he published an article entitled “How to Suck Off a Star,” in which he named a Hollywood star who he implied participated in oral sex with him in exchange for a story. The post, like Ms. Finnegan’s, was quietly taken down from the Entertainment Weekly website, and the company recently reached a settlement with the estate of Jason Robards.

Since his very public firing last summer, Mr. Moylan has been unable to find work as an entertainment writer, although he is able to make ends meet by doing freelance work, writing advertising copy for websites. “‘It always helps to be flexible,’” Mr. Moylan said, reading from one yoga studio site. “Do you think they know that I mean that sexually? Probably not. People are so stupid. It’s going to blow their minds next month, when I mention that certain exercises make it easy to fist.”

“Have you heard about fisting?” Mr. Moylan asked, before launching into a graphic description, complete with photos that he had posted on the website of an assisted living facility he recently wrote for.

As for Ms. Finnegan, the future is even less clear. With her severance package from Gawker long since spent and no job prospects on the horizon, she is faced, like many former Gawker employees of her generation, with a choice: grow the hell up or do something else with her life. For now, her main goal is finding a new place to stay and a new job. When asked what she would be willing to do, she laughed out loud, although without any trace of joy.

“Whatever,” she said, looking out the window. “Whatever.”

Correction: An earlier version of this story referred to Brian Moylan as “Bryan.” We apologize for the error, and hope that Mr. Moylan will stop calling.